NPASS Compound

Structure

NPC103816 OpenBabel07101718202D 45 50 0 0 1 0 0 0 0 0999 V2000 4.9020 0.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 0.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4303 3.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3737 3.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0850 0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2680 -0.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2680 -4.7170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7190 1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7190 -0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7190 -1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7190 2.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9020 0.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4510 1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2680 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2680 2.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8170 1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2680 -2.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9020 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4510 1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4510 0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9020 -1.8868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0850 -0.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2680 0.9434 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4510 2.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 1.8868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8170 0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0850 -3.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0850 2.3585 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2680 -1.8868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8170 0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8170 1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9020 -2.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9020 2.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0850 1.4151 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0850 -1.4151 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6340 2.8302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 2.8302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.8302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4510 -1.4151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7190 -3.3019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2680 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0850 -4.2453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 2 0 0 0 0 3 35 1 0 0 0 0 4 35 1 0 0 0 0 6 43 1 0 0 0 0 7 44 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 19 2 0 0 0 0 10 22 1 0 0 0 0 11 35 1 0 0 0 0 12 36 1 0 0 0 0 13 21 2 0 0 0 0 13 26 1 0 0 0 0 14 21 1 0 0 0 0 14 28 2 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 16 30 1 0 0 0 0 17 27 1 0 0 0 0 17 32 2 0 0 0 0 18 29 2 0 0 0 0 18 31 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 43 1 0 0 0 0 22 34 1 0 0 0 0 22 37 1 1 0 0 0 23 37 1 6 0 0 0 24 36 1 1 0 0 0 25 38 2 0 0 0 0 26 33 2 0 0 0 0 26 39 1 0 0 0 0 27 33 1 0 0 0 0 27 40 2 0 0 0 0 28 33 1 0 0 0 0 28 45 1 0 0 0 0 29 34 1 0 0 0 0 29 44 1 0 0 0 0 30 35 1 0 0 0 0 30 36 1 1 0 0 0 31 37 1 0 0 0 0 31 41 2 0 0 0 0 32 45 1 0 0 0 0 34 42 2 0 0 0 0 36 5 1 1 0 0 0 37 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.29
Volume:	638.49
LogP:	5.135
LogD:	2.452
LogS:	-3.785
# Rotatable Bonds:	5
TPSA:	120.11
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.371
Fsp3:	0.514
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.142
MDCK Permeability:	1.5280038496712223e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.132

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	91.33644104003906%
Volume Distribution (VD):	0.974
Pgp-substrate:	4.200850963592529%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.284
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.206
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.589
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.894

ADMET: Excretion

Clearance (CL):	11.414
Half-life (T1/2):	0.21

ADMET: Toxicity

hERG Blockers:	0.212
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.419
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.505
Carcinogencity:	0.79
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.987

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC103816

Natural Product ID:	NPC103816
*Common Name:**	Dichrostachine M
IUPAC Name:	(4aR,8R,8aS)-8-[[(1R,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3-oxo-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl]-8a-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-3-methoxy-7-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
Synonyms:	Dichrostachine M
Standard InCHIKey:	NWFRZQVUFDCHQD-CTGSLWKSSA-N
Standard InCHI:	InChI=1S/C37H42O8/c1-19-9-10-22-34(42)29(44-7)18-31(41)37(22,32-17-27(40)33-26(39)13-21(43-6)14-28(33)45-32)23(19)15-24-20(2)25(38)16-30-35(3,4)11-8-12-36(24,30)5/h9,13-14,17-18,22-24,30,39H,2,8,10-12,15-16H2,1,3-7H3/t22-,23+,24-,30-,36+,37-/m0/s1
SMILES:	COC1=CC(=O)[C@@]2([C@H](C1=O)CC=C([C@H]2C[C@H]1C(=C)C(=O)C[C@@H]2[C@]1(C)CCCC2(C)C)C)c1cc(=O)c2c(o1)cc(cc2O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077625
PubChem CID:	44557283
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15669	Dichrostachys cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19761234]
NPO15669	Dichrostachys cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	3.1	uM	PMID[522558]
NPT2	Others	Unspecified		IC50	=	3000.0	nM	PMID[522558]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC103816 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	460
0.1-0.2	1741
0.2-0.3	3496
0.3-0.4	8548
0.4-0.5	10392
0.5-0.6	5217
0.6-0.7	5601
0.7-0.8	5937
0.8-0.85	1208
0.85-0.9	79
0.9-0.95	8
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC61382
0.9744	High Similarity	NPC17274
0.9744	High Similarity	NPC85047
0.9744	High Similarity	NPC120857
0.962	High Similarity	NPC20734
0.962	High Similarity	NPC286074
0.962	High Similarity	NPC54903
0.956	High Similarity	NPC193698
0.9441	High Similarity	NPC469393
0.9367	High Similarity	NPC469395
0.9161	High Similarity	NPC470353
0.913	High Similarity	NPC469394
0.9108	High Similarity	NPC470354
0.9108	High Similarity	NPC192587
0.9108	High Similarity	NPC470352
0.9079	High Similarity	NPC472447
0.9079	High Similarity	NPC472446
0.9062	High Similarity	NPC475106
0.9013	High Similarity	NPC473812
0.9013	High Similarity	NPC473813
0.8987	High Similarity	NPC56049
0.8987	High Similarity	NPC54830
0.8951	High Similarity	NPC314653
0.8951	High Similarity	NPC316262
0.8875	High Similarity	NPC90497
0.8841	High Similarity	NPC193222
0.8824	High Similarity	NPC204469
0.882	High Similarity	NPC195136
0.8812	High Similarity	NPC474637
0.878	High Similarity	NPC476255
0.878	High Similarity	NPC476056
0.8758	High Similarity	NPC105584
0.8735	High Similarity	NPC313717
0.8735	High Similarity	NPC315306
0.8734	High Similarity	NPC305965
0.8712	High Similarity	NPC94796
0.8704	High Similarity	NPC475107
0.8704	High Similarity	NPC43490
0.8704	High Similarity	NPC472618
0.8704	High Similarity	NPC121647
0.8704	High Similarity	NPC313368
0.8696	High Similarity	NPC201127
0.8683	High Similarity	NPC477529
0.8679	High Similarity	NPC154683
0.8679	High Similarity	NPC40356
0.8671	High Similarity	NPC188403
0.8667	High Similarity	NPC62444
0.8662	High Similarity	NPC470460
0.8659	High Similarity	NPC131578
0.8654	High Similarity	NPC178343
0.8654	High Similarity	NPC329678
0.8654	High Similarity	NPC5820
0.8654	High Similarity	NPC306488
0.865	High Similarity	NPC476929
0.8645	High Similarity	NPC11700
0.8645	High Similarity	NPC158874
0.8642	High Similarity	NPC15815
0.8642	High Similarity	NPC472617
0.8642	High Similarity	NPC125969
0.8642	High Similarity	NPC295090
0.8636	High Similarity	NPC232021
0.8636	High Similarity	NPC40118
0.8636	High Similarity	NPC126534
0.8631	High Similarity	NPC475080
0.8625	High Similarity	NPC214632
0.8625	High Similarity	NPC324447
0.8623	High Similarity	NPC476196
0.8616	High Similarity	NPC178484
0.8616	High Similarity	NPC81474
0.8614	High Similarity	NPC223413
0.8614	High Similarity	NPC470377
0.8614	High Similarity	NPC478059
0.8614	High Similarity	NPC76647
0.8614	High Similarity	NPC478060
0.8614	High Similarity	NPC471975
0.8614	High Similarity	NPC470374
0.8608	High Similarity	NPC470461
0.8608	High Similarity	NPC471114
0.8599	High Similarity	NPC259632
0.859	High Similarity	NPC273538
0.859	High Similarity	NPC326500
0.859	High Similarity	NPC216538
0.859	High Similarity	NPC476055
0.859	High Similarity	NPC117716
0.859	High Similarity	NPC470674
0.859	High Similarity	NPC234629
0.859	High Similarity	NPC311741
0.859	High Similarity	NPC470673
0.8589	High Similarity	NPC286422
0.8589	High Similarity	NPC226462
0.8589	High Similarity	NPC98023
0.8581	High Similarity	NPC325346
0.8581	High Similarity	NPC297600
0.858	High Similarity	NPC272196
0.858	High Similarity	NPC271741
0.858	High Similarity	NPC257166
0.858	High Similarity	NPC287789
0.858	High Similarity	NPC1796
0.8571	High Similarity	NPC100049
0.8571	High Similarity	NPC14606
0.8571	High Similarity	NPC205026
0.8571	High Similarity	NPC52611
0.8571	High Similarity	NPC215203
0.8571	High Similarity	NPC159707
0.8571	High Similarity	NPC265178
0.8571	High Similarity	NPC158027
0.8571	High Similarity	NPC79375
0.8571	High Similarity	NPC186227
0.8571	High Similarity	NPC150908
0.8571	High Similarity	NPC265624
0.8571	High Similarity	NPC118128
0.8571	High Similarity	NPC37253
0.8571	High Similarity	NPC121649
0.8571	High Similarity	NPC248739
0.8571	High Similarity	NPC476159
0.8563	High Similarity	NPC41598
0.8563	High Similarity	NPC63514
0.8563	High Similarity	NPC55422
0.8563	High Similarity	NPC40089
0.8563	High Similarity	NPC476146
0.8563	High Similarity	NPC158329
0.8563	High Similarity	NPC47634
0.8563	High Similarity	NPC75141
0.8563	High Similarity	NPC476216
0.8562	High Similarity	NPC25427
0.8554	High Similarity	NPC125465
0.8554	High Similarity	NPC251336
0.8553	High Similarity	NPC29777
0.8553	High Similarity	NPC471115
0.8545	High Similarity	NPC476931
0.8544	High Similarity	NPC152233
0.8544	High Similarity	NPC39195
0.8544	High Similarity	NPC145467
0.8544	High Similarity	NPC296869
0.8544	High Similarity	NPC244407
0.8544	High Similarity	NPC266572
0.8537	High Similarity	NPC219686
0.8537	High Similarity	NPC189552
0.8537	High Similarity	NPC273467
0.8535	High Similarity	NPC477955
0.8535	High Similarity	NPC473135
0.8535	High Similarity	NPC124729
0.8535	High Similarity	NPC470676
0.8535	High Similarity	NPC470458
0.8535	High Similarity	NPC473132
0.8535	High Similarity	NPC299011
0.8528	High Similarity	NPC18699
0.8528	High Similarity	NPC55443
0.8528	High Similarity	NPC228654
0.8528	High Similarity	NPC51247
0.8526	High Similarity	NPC293053
0.8526	High Similarity	NPC212932
0.8526	High Similarity	NPC9117
0.8526	High Similarity	NPC19896
0.8526	High Similarity	NPC24821
0.8526	High Similarity	NPC190637
0.8521	High Similarity	NPC476229
0.8521	High Similarity	NPC474276
0.8521	High Similarity	NPC73899
0.8521	High Similarity	NPC17105
0.8521	High Similarity	NPC147363
0.8521	High Similarity	NPC471969
0.8521	High Similarity	NPC476152
0.8521	High Similarity	NPC476139
0.8519	High Similarity	NPC309648
0.8519	High Similarity	NPC32867
0.8519	High Similarity	NPC198489
0.8519	High Similarity	NPC61112
0.8516	High Similarity	NPC136840
0.8516	High Similarity	NPC282300
0.8516	High Similarity	NPC262094
0.8516	High Similarity	NPC90582
0.8516	High Similarity	NPC110969
0.8509	High Similarity	NPC71061
0.8509	High Similarity	NPC329844
0.8509	High Similarity	NPC290830
0.8509	High Similarity	NPC303485
0.8509	High Similarity	NPC121568
0.8509	High Similarity	NPC194593
0.8509	High Similarity	NPC72425
0.8506	High Similarity	NPC49242
0.8503	High Similarity	NPC286230
0.8503	High Similarity	NPC253730
0.85	High Similarity	NPC478148
0.85	High Similarity	NPC476162
0.8494	Intermediate Similarity	NPC169471
0.8494	Intermediate Similarity	NPC189689
0.8491	Intermediate Similarity	NPC65775
0.8491	Intermediate Similarity	NPC65589
0.8491	Intermediate Similarity	NPC288036
0.8491	Intermediate Similarity	NPC97029
0.8491	Intermediate Similarity	NPC291746
0.8491	Intermediate Similarity	NPC10027
0.8491	Intermediate Similarity	NPC158338
0.8491	Intermediate Similarity	NPC100985
0.8491	Intermediate Similarity	NPC269420
0.8491	Intermediate Similarity	NPC288840
0.8491	Intermediate Similarity	NPC97028
0.8485	Intermediate Similarity	NPC473022
0.8481	Intermediate Similarity	NPC14001

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC103816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	990
0.2-0.3	1709
0.3-0.4	2691
0.4-0.5	2073
0.5-0.6	878
0.6-0.7	274
0.7-0.8	123
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7075	Discontinued
0.8282	Intermediate Similarity	NPD7819	Suspended
0.8235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6599	Discontinued
0.8204	Intermediate Similarity	NPD6959	Discontinued
0.8171	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7411	Suspended
0.8153	Intermediate Similarity	NPD2800	Approved
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8117	Intermediate Similarity	NPD6651	Approved
0.811	Intermediate Similarity	NPD6801	Discontinued
0.8101	Intermediate Similarity	NPD3750	Approved
0.8098	Intermediate Similarity	NPD4380	Phase 2
0.8089	Intermediate Similarity	NPD1549	Phase 2
0.8077	Intermediate Similarity	NPD2796	Approved
0.8072	Intermediate Similarity	NPD7768	Phase 2
0.8025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD1607	Approved
0.7987	Intermediate Similarity	NPD1240	Approved
0.7975	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3882	Suspended
0.7962	Intermediate Similarity	NPD6100	Approved
0.7962	Intermediate Similarity	NPD6099	Approved
0.7953	Intermediate Similarity	NPD6166	Phase 2
0.7953	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6799	Approved
0.7917	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1512	Approved
0.7844	Intermediate Similarity	NPD2801	Approved
0.7844	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7808	Phase 3
0.7836	Intermediate Similarity	NPD6232	Discontinued
0.7805	Intermediate Similarity	NPD5403	Approved
0.7798	Intermediate Similarity	NPD3817	Phase 2
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3748	Approved
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.773	Intermediate Similarity	NPD1511	Approved
0.7727	Intermediate Similarity	NPD6797	Phase 2
0.7711	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD5402	Approved
0.7683	Intermediate Similarity	NPD2534	Approved
0.7683	Intermediate Similarity	NPD2532	Approved
0.7683	Intermediate Similarity	NPD5401	Approved
0.7683	Intermediate Similarity	NPD2533	Approved
0.7679	Intermediate Similarity	NPD1934	Approved
0.7667	Intermediate Similarity	NPD8434	Phase 2
0.7647	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7616	Intermediate Similarity	NPD5494	Approved
0.7614	Intermediate Similarity	NPD7054	Approved
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2344	Approved
0.7571	Intermediate Similarity	NPD7472	Approved
0.7571	Intermediate Similarity	NPD7074	Phase 3
0.7562	Intermediate Similarity	NPD2799	Discontinued
0.7557	Intermediate Similarity	NPD3818	Discontinued
0.7546	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5953	Discontinued
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7486	Intermediate Similarity	NPD3926	Phase 2
0.7485	Intermediate Similarity	NPD1243	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7458	Intermediate Similarity	NPD3751	Discontinued
0.7444	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.7439	Intermediate Similarity	NPD7003	Approved
0.7416	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8313	Approved
0.7403	Intermediate Similarity	NPD8312	Approved
0.7394	Intermediate Similarity	NPD2309	Approved
0.7391	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7381	Intermediate Similarity	NPD920	Approved
0.7362	Intermediate Similarity	NPD1471	Phase 3
0.7356	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1465	Phase 2
0.7326	Intermediate Similarity	NPD5761	Phase 2
0.7326	Intermediate Similarity	NPD5760	Phase 2
0.7318	Intermediate Similarity	NPD7286	Phase 2
0.7301	Intermediate Similarity	NPD2935	Discontinued
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7296	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6559	Discontinued
0.7292	Intermediate Similarity	NPD7435	Discontinued
0.7292	Intermediate Similarity	NPD7697	Approved
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7698	Approved
0.7273	Intermediate Similarity	NPD1247	Approved
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2798	Approved
0.7257	Intermediate Similarity	NPD919	Approved
0.7256	Intermediate Similarity	NPD2346	Discontinued
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.7247	Intermediate Similarity	NPD2403	Approved
0.7246	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6779	Approved
0.7225	Intermediate Similarity	NPD6776	Approved
0.7225	Intermediate Similarity	NPD6781	Approved
0.7225	Intermediate Similarity	NPD6778	Approved
0.7225	Intermediate Similarity	NPD6780	Approved
0.7225	Intermediate Similarity	NPD6777	Approved
0.7225	Intermediate Similarity	NPD6782	Approved
0.7197	Intermediate Similarity	NPD1470	Approved
0.7194	Intermediate Similarity	NPD8151	Discontinued
0.7188	Intermediate Similarity	NPD3268	Approved
0.7184	Intermediate Similarity	NPD4288	Approved
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7135	Intermediate Similarity	NPD5711	Approved
0.7135	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD8166	Discontinued
0.7121	Intermediate Similarity	NPD7801	Approved
0.7118	Intermediate Similarity	NPD6273	Approved
0.7115	Intermediate Similarity	NPD3972	Approved
0.7099	Intermediate Similarity	NPD943	Approved
0.7095	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1203	Approved
0.7089	Intermediate Similarity	NPD2797	Approved
0.7077	Intermediate Similarity	NPD8319	Approved
0.7077	Intermediate Similarity	NPD8320	Phase 1
0.707	Intermediate Similarity	NPD4749	Approved
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.7047	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7229	Phase 3
0.7031	Intermediate Similarity	NPD7700	Phase 2
0.7031	Intermediate Similarity	NPD7699	Phase 2
0.703	Intermediate Similarity	NPD4308	Phase 3
0.703	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4287	Approved
0.7016	Intermediate Similarity	NPD4361	Phase 2
0.7016	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD9717	Approved
0.6988	Remote Similarity	NPD5404	Approved
0.6988	Remote Similarity	NPD5405	Approved
0.6988	Remote Similarity	NPD5406	Approved
0.6988	Remote Similarity	NPD5408	Approved
0.6983	Remote Similarity	NPD8127	Discontinued
0.6978	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7228	Approved
0.6977	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3764	Approved
0.6971	Remote Similarity	NPD37	Approved
0.6966	Remote Similarity	NPD6234	Discontinued
0.6964	Remote Similarity	NPD2654	Approved
0.6963	Remote Similarity	NPD6534	Approved
0.6963	Remote Similarity	NPD6535	Approved
0.6951	Remote Similarity	NPD6355	Discontinued
0.6951	Remote Similarity	NPD5124	Phase 1
0.6951	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4967	Phase 2
0.6949	Remote Similarity	NPD4966	Approved
0.6949	Remote Similarity	NPD4965	Approved
0.6943	Remote Similarity	NPD422	Phase 1
0.6943	Remote Similarity	NPD1201	Approved
0.6943	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7236	Approved
0.6933	Remote Similarity	NPD8032	Phase 2
0.6928	Remote Similarity	NPD7033	Discontinued
0.6919	Remote Similarity	NPD6104	Discontinued
0.6914	Remote Similarity	NPD4625	Phase 3
0.6914	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1548	Phase 1
0.6893	Remote Similarity	NPD2296	Approved
0.6893	Remote Similarity	NPD7907	Approved
0.6889	Remote Similarity	NPD7199	Phase 2
0.6875	Remote Similarity	NPD3266	Approved
0.6875	Remote Similarity	NPD3267	Approved
0.6871	Remote Similarity	NPD6798	Discontinued
0.6866	Remote Similarity	NPD7783	Phase 2
0.6866	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD230	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data